Methyl 4-benzyl-2-oxo-oxazolidine-5-carboxylate → methyl (4S,5R)-4-benzyl-2-oxo-oxazolidine-5-carboxylate

HRID 1379223Notes

Reaction equation

[CH2:1]([CH:8]1[CH:12]([C:13]([O:15][CH3:16])=[O:14])[O:11][C:10](=[O:17])[NH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C1COCC1>[CH2:1]([C@H:8]1[C@H:12]([C:13]([O:15][CH3:16])=[O:14])[O:11][C:10](=[O:17])[NH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 45 °C

Procedure

A solution of 70.0 g of a 92:8 mixture of the (4S,5S)- and (4S,5R)-isomers of methyl 4-benzyl-2-oxo-oxazolidine-5-carboxylate and 7.0 g of potassium tert.butylate in 700 ml of THF was stirred at 20° C. for four hours and at 45° C. for 2 hours, the solution was washed twice with semi-saturated sodium chloride solution, dried over MgSO4, filtered and the filtrate was evaporated to give 68 g (97%) of 95% methyl (4S,5R)-4-benzyl-2-oxo-oxazolidine-5-carboxylate (tlc (SiO2, ethyl acetate):Rf =0.5).

Workup

washthe solution was washed twice with semi-saturated sodium chloride solution
dry with materialdried over MgSO4
filtrationfiltered
customthe filtrate was evaporated

Sources & evidence

ORD record: ord-0b3e2972a0704a46ad83aa8fa21da8da
Source dataset: uspto-grants-1997_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05670653

Reaction notes

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